A waterfront with a pier, calm water, and houses with palm trees in the background.

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Check availability on Sugarloaf Key Adventure Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Sugarloaf Key adventure hotels

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A sunset view with a thatched structure and a palm tree by a calm body of water.
A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.

1. Parmer's Resort

Parmer's Resort
Summerland Key
United States
Mireya
AED 465
AED 643 total
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.

2. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
United States
Elena S.
AED 459
AED 1,518 total
includes taxes & fees
4 Oct - 5 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Sport court
Outdoor dining
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

3. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
United States
Cheryl V.
AED 579
AED 1,667 total
includes taxes & fees
4 Oct - 5 Oct
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A waterfront property with a covered porch, a boat dock, and a clear sky.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.
A bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.

4. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
United States
Mckayla S.
AED 1,355
AED 2,606 total
includes taxes & fees
1 Nov - 2 Nov
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.
A modern kitchen with built-in appliances, a dining area with a wooden table and chairs, and a cozy bedroom with a bed and a view of the outdoors.
An outdoor patio with a table and chairs, a pergola with hanging lights, and a white fence.
A bedroom with a bed, a chair, a nightstand, a painting, and a window with blinds.

5. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
United States
John B.
AED 808
AED 1,969 total
includes taxes & fees
11 Oct - 12 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage
Pool
Beach
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
A covered outdoor area with wicker furniture and string lights.

6. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
United States
jim b.
AED 636
AED 1,743 total
includes taxes & fees
4 Oct - 5 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, a marina, and a flag.
A marina with boats docked, a clear sky, and a calm waterway.
Outdoor dining

7. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
United States
Tammy G.
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, a marina, and a flag.
Outdoor dining

8. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
United States
Nora Kay F.
AED 675
AED 1,790 total
includes taxes & fees
4 Oct - 5 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Pool
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.

9. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
AED 434
AED 695 total
includes taxes & fees
5 Oct - 6 Oct
Blue Flamingo Resort Key West
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

10. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
AED 428
AED 706 total
includes taxes & fees
26 Oct - 27 Oct
The Perry Hotel & Marina Key West
View all properties

Top Sugarloaf Key Hotel Reviews

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent
"K"
Manuel 2-night trip
Posted less than an hour ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location and clean room! Easy to walk to restaurants, bars, and Mallory Square. The Chart Room Cocktail Lounge in hotel was also a fun late night stop."
Jennifer 2-night trip
Posted 1 hour ago
Pier House Resort & Spa
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"This was our second time to stay here and this place never disappoints. Staff is wonderful too"
Jonathan 4-night trip
Posted 2 hours ago
Hilton Key West Resort & Marina
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"very nice..."
RICHARD 1-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Wonderful"
James 2-night trip
Posted 13 hours ago
Hampton Inn Key West FL
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Amazing!"
Naomi 2-night trip
Posted 17 hours ago
Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Staff was very nice. Pool was great as well as the hot tub."
Cana 1-night trip
Posted 18 hours ago
Hilton Garden Inn Key West / The Keys Collection
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"
Alexandre 1-night trip
Posted 2 days ago
Parrot Key Hotel & Villas

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